Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction

Masayuki Utsugi, Yasuaki Kamada, Hidetoshi Miyamoto, Masahisa Nakada

    Research output: Contribution to journalArticle

    12 Citations (Scopus)

    Abstract

    Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction is described. A conjugate addition of cyanide to enone 17 proceeded diastereoselectively to provide the desired 18 incorporating the correct C3 stereogenic center in the taxol C-ring. The intramolecular B-alkyl Suzuki-Miyaura coupling reaction of 22, which was derived from 18, successfully furnished the taxol B-ring in 81% yield.

    Original languageEnglish
    Pages (from-to)6868-6872
    Number of pages5
    JournalTetrahedron Letters
    Volume48
    Issue number39
    DOIs
    Publication statusPublished - 2007 Sep 24

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    Cyanides
    Skeleton
    Paclitaxel
    taxane
    cephalomannine

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction. / Utsugi, Masayuki; Kamada, Yasuaki; Miyamoto, Hidetoshi; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 48, No. 39, 24.09.2007, p. 6868-6872.

    Research output: Contribution to journalArticle

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    AU - Miyamoto, Hidetoshi

    AU - Nakada, Masahisa

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